Hydrochloric Acid → HCID 178515143、化合物

HRID 853706

反応式

HRID 853706 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[CH2:13][CH2:12][C:11]2=[O:16])=[CH:4][CH:3]=1.C[O:18][C:19]([C:21]1[C:26]([C:27](OC)=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1)=O.[H-].[Na+].Cl>O1CCCC1.C(OCC)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]2[C:14](=[O:15])[C:13]3[C:19]([OH:18])=[C:21]4[C:26]([CH:25]=[CH:24][CH:23]=[N:22]4)=[C:27]([OH:28])[C:12]=3[C:11]2=[O:16])=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 690582,3-Dimethyl 2,3-pyridinedicarboxylateHCID 589289521-[2-(4-Fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione

生成物 1

HCID 178515143HCID 178515143、化合物収率 58%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To 1-[2-(4-Fluoro-phenyl)-ethyl]-pyrrolidine-2,5-dione 309 (270 mg, 1.22 mmol and pyridine-2,3-dicarboxylic acid dimethyl ester (261.6 mg, 1.34 mmol) dissolved in tetrahydrofuran (12.0 ml) and methanol (1.4 ml) was added a 60% dispersion of sodium hydride in mineral oil (108 mg, 2.7 mmol). The reaction mixture was warmed to 80° C. and kept at 80° C. with stirring overnight. The reaction mixture was then placed in an ice bath and titrated to a pH of 4 with 1 M HCl. Two hundred (200) ml of diethylether was then added and the resulting yellow solid was collected by filtration. The solid was washed twice with ether, twice with water, and dried under high vacuum with heating to provide 7-[2-(4-fluoro-phenyl)-ethyl]-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione 310 (250 mg, 0.71 mmol, 58%). 1H NMR (d-DMSO) δ 10.7 (broad, 1H), 8.98 (dd, 1H), 8.66 (dd, 1H), 7.73 (m, 1H), 7.18 (m, 2H), 7.04 (t, 2H), 3.72 (t, 2H), 2.86 (t, 2H). MS: 353.1 (M+1).

後処理

  1. customkept at 80° C.
  2. customThe reaction mixture was then placed in an ice bath
  3. filtrationthe resulting yellow solid was collected by filtration
  4. washThe solid was washed twice with ether, twice with water
  5. customdried under high vacuum
  6. temperaturewith heating

出典と根拠

ORDレコード
ord-9803244f792e4dc5b3604b85b4a2777d
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

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